DE2518984B1 - Verfahren zur herstellung von n-acetoacetyl-2,5-dimethoxy-4-chlor- anilid - Google Patents
Verfahren zur herstellung von n-acetoacetyl-2,5-dimethoxy-4-chlor- anilidInfo
- Publication number
- DE2518984B1 DE2518984B1 DE19752518984 DE2518984A DE2518984B1 DE 2518984 B1 DE2518984 B1 DE 2518984B1 DE 19752518984 DE19752518984 DE 19752518984 DE 2518984 A DE2518984 A DE 2518984A DE 2518984 B1 DE2518984 B1 DE 2518984B1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- dimethoxy
- diketene
- acetoacetyl
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 16
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752518984 DE2518984B1 (de) | 1975-04-29 | 1975-04-29 | Verfahren zur herstellung von n-acetoacetyl-2,5-dimethoxy-4-chlor- anilid |
| ES447297A ES447297A1 (es) | 1975-04-29 | 1976-04-23 | Procedimiento para la preparacion den-acetoacetil-2,5-dime- toxi-4-cloroanilina. |
| US05/680,670 US4042622A (en) | 1975-04-29 | 1976-04-27 | Process for the preparation of N-acetoacetyl-2,5-dimethoxy-4-chloroanilide |
| IN736/CAL/76A IN144221B (enrdf_load_stackoverflow) | 1975-04-29 | 1976-04-27 | |
| BR2623/76A BR7602623A (pt) | 1975-04-29 | 1976-04-28 | Processo para a preparacao de nacetoacetil-2,5-dimetoxi-4-cloroanilida |
| JP51047932A JPS51131840A (en) | 1975-04-29 | 1976-04-28 | Process for preparing nnacetoacetyll2*55 dimethoxyy44chloroanilide |
| AU13408/76A AU496793B2 (en) | 1975-04-29 | 1976-04-28 | Process forthe preparation of n-acetoacetyl-2, 5-dimethoxy-4 chloroanilide |
| FR7612715A FR2309516A1 (fr) | 1975-04-29 | 1976-04-29 | Procede de preparation du n-acetoacetyl-2,5-dimethoxy-4-chloranilide |
| GB1748576A GB1476919A (en) | 1975-04-29 | 1976-04-29 | Process for the preparation of n-acetoacetyl-2,5-dimethoxy- 4-chloroanilide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752518984 DE2518984B1 (de) | 1975-04-29 | 1975-04-29 | Verfahren zur herstellung von n-acetoacetyl-2,5-dimethoxy-4-chlor- anilid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2518984B1 true DE2518984B1 (de) | 1976-10-21 |
Family
ID=5945274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752518984 Withdrawn DE2518984B1 (de) | 1975-04-29 | 1975-04-29 | Verfahren zur herstellung von n-acetoacetyl-2,5-dimethoxy-4-chlor- anilid |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4042622A (enrdf_load_stackoverflow) |
| JP (1) | JPS51131840A (enrdf_load_stackoverflow) |
| AU (1) | AU496793B2 (enrdf_load_stackoverflow) |
| BR (1) | BR7602623A (enrdf_load_stackoverflow) |
| DE (1) | DE2518984B1 (enrdf_load_stackoverflow) |
| ES (1) | ES447297A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2309516A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1476919A (enrdf_load_stackoverflow) |
| IN (1) | IN144221B (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001994A1 (de) * | 1977-11-04 | 1979-05-30 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Acetoacetylaminobenzolen |
| EP0053713A1 (de) * | 1980-12-09 | 1982-06-16 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von 1-Acetoacetylamino-4-chlor-2,5-dimethoxybenzol |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1982675A (en) * | 1934-12-04 | Pbeparation of acetoacetanilid | ||
| US3121743A (en) * | 1964-02-18 | Production of aceto-acetarylamides | ||
| US2714117A (en) * | 1955-07-26 | Production of acetoacetic acid amides | ||
| US2174239A (en) * | 1936-03-05 | 1939-09-26 | Standard Oil Dev Co | Preparing acetyl acetic acid derivatives |
| US2152132A (en) * | 1936-12-12 | 1939-03-28 | Carbide & Carbon Chem Corp | Acetoacetyl amides and process for their preparation |
| CH277023A (de) * | 1949-05-03 | 1951-08-15 | Ciba Geigy | Verfahren zur Herstellung eines Zwischenproduktes. |
| BE513633A (enrdf_load_stackoverflow) | 1951-08-21 | |||
| US2913495A (en) * | 1957-03-25 | 1959-11-17 | Union Carbide Corp | Stabilization of arylamines |
| US3063899A (en) * | 1958-02-22 | 1962-11-13 | Hoechst Ag | beta-hydroxybutyric acid-cyclohexylamide and a process of preparing it |
| FR1297062A (fr) * | 1961-08-09 | 1962-06-22 | Distillers Co Yeast Ltd | Procédé de préparation d'acétoacétyl-arylamides |
| US3304328A (en) * | 1963-10-25 | 1967-02-14 | Fmc Corp | Preparation of acetoacetarylamides |
-
1975
- 1975-04-29 DE DE19752518984 patent/DE2518984B1/de not_active Withdrawn
-
1976
- 1976-04-23 ES ES447297A patent/ES447297A1/es not_active Expired
- 1976-04-27 US US05/680,670 patent/US4042622A/en not_active Expired - Lifetime
- 1976-04-27 IN IN736/CAL/76A patent/IN144221B/en unknown
- 1976-04-28 AU AU13408/76A patent/AU496793B2/en not_active Expired
- 1976-04-28 BR BR2623/76A patent/BR7602623A/pt unknown
- 1976-04-28 JP JP51047932A patent/JPS51131840A/ja active Pending
- 1976-04-29 FR FR7612715A patent/FR2309516A1/fr active Granted
- 1976-04-29 GB GB1748576A patent/GB1476919A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0001994A1 (de) * | 1977-11-04 | 1979-05-30 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Acetoacetylaminobenzolen |
| EP0053713A1 (de) * | 1980-12-09 | 1982-06-16 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von 1-Acetoacetylamino-4-chlor-2,5-dimethoxybenzol |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2309516B1 (enrdf_load_stackoverflow) | 1979-06-15 |
| FR2309516A1 (fr) | 1976-11-26 |
| GB1476919A (en) | 1977-06-16 |
| JPS51131840A (en) | 1976-11-16 |
| US4042622A (en) | 1977-08-16 |
| BR7602623A (pt) | 1976-11-23 |
| AU496793B2 (en) | 1978-10-26 |
| ES447297A1 (es) | 1977-06-16 |
| AU1340876A (en) | 1977-11-03 |
| IN144221B (enrdf_load_stackoverflow) | 1978-04-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |